He starts a screen-printing business and sells T-shirts on accident and it becomes a million-dollar company. He then house hacks a few office buildings successfully before talking about his main focus, a company called Million Dollar Collar that he started.

What Happens When You Double Down On An Innovative Idea, With Rob Kessler

Key Points on What Happens When You Double Down On An Innovative Business Idea

clothing business
Photographer: Jacek Dylag | Source: Unsplash
  • Rob started his career in the family diamond business helping his father sell diamonds.
  • In 2006, he got into real estate investing.
  • Soon the market started to slow down, so he decided to work with artists and sell their art on T-shirts.
  • However, using screenprinting companies was too expensive. So he bought a printer and eventually built a million-dollar business from his basement.
  • He and his wife soon outgrow their house and purchased a 6,000 sq ft property. They were able to divide it into offices and rent some out for cash flow.
  • Rob had a clothing line too, called NEWD. Eventually, as the T-shirt business became very successful, he left NEWD behind and focused on the printing.
  • Eventually, he and his wife sold their house and moved to LA. They bought an older building for $200k and transformed it to 22 offices. With all the improvements they put in, they were able to sell it for 3 times the price in 13 months.
  • Rob invested the money into a yacht charter business as he is a captain.
  • He invented a product that can substitute ties, the Million Dollar Collar. It is a piece of plastic that helps the collar to stay crisp.
  • It took him 3 years and 100 ruined shirts until he perfected the design, but they sold almost 300k units in the last 3-4 years since they launched.
  • The patenting process took 2.5 years and cost over 6 figures. Finally, he is breaking even and can generate profit.
  • Rob made an agreement with around 600 drycleaners all around the US who can install the plastic into the collar. It can be sewn in at home too.
  • In the future, he wants to get into real estate investing again.
Moments of Truth with Rob Kessler
  • Who is your success role model? His dad.
  • What is your biggest success? His marriage.
  • What does a typical day look like for you? He is trying to be more disciplined with his time recently. He writes down his schedule in 30-minute intervals and plans his day around it.
  • What’s your favorite quote? “Do more for others than they expect.” – Wilt Chamberlain
  • What are your hobbies? He likes playing volleyball
  • What is the best business book you’ve read? Grant Cardone – If You’re Not First, You’re Last
  • If there was one key piece of advice you could leave our listeners with about achieving success, what would it be? Keep going and don’t quit, because you only fail if you quit.

About our Guest, Rob Kessler

Rob Kessler

Rob Kessler is the inventor of Million Dollar Collar, a relatively simple solution to fix what his company dubs "Placketitis" The sinking, wrinkling, and folding of the placket of a casually worn dress shirt. He also, co-founder of goTIELESS the first shirts designed to be worn tieless, with Million Dollar Collar already built-in and head Captain at Bella Boating.

Prior to Million Dollar Collar, Rob built a screen printing and embroidery business from a spare bedroom in his house to over $1,000,000 in revenue before selling the company. Although the company was never intended to be a screen printing company, word soon spread about the high quality, great pricing and never miss a deadline guarantee.

Rob's sales experience in a number of high dollar industries including Diamonds, Real Estate and Automotive Sales provided a unique blend of backgrounds to transition him into the fashion world. His ability to look at the world through a different set of lenses than most people lead to his success in every sales job and with both of his own businesses.